Pyridine N-oxides as HAT reagents for photochemical C–H functionalization of electron-deficient heteroarenes?

Chemical Communications Pub Date: 2022-08-24 DOI: 10.1039/D2CC03772F

Abstract

Pyridine N-oxides have only recently marked their presence in the photocatalysis field, mainly serving as oxypyridinium salt precursors. Herein, their unique reactivity as a hydrogen atom transfer reagent in photochemical, Minisci-type alkylation of electron-deficient heteroarenes is unveiled. The formation of an EDA complex between a heterocyclic substrate and N-oxide precludes the need for a photocatalyst. The developed method allows for a broad range of radical precursors to be used, namely alkanes, alkenes, amides, and ethers, for efficient alkylation of azines.

Graphical abstract: Pyridine N-oxides as HAT reagents for photochemical C–H functionalization of electron-deficient heteroarenes
Recommended Literature